The syntheses of new classes of oligocarbamates with differing substitution patterns towards the identification of novel folding patterns are proposed, which should ultimately lead to rational control of biological activity. A flexible synthetic route to oligocarbamates using the asymmetric reactions of epoxides to generate monomers and solid phase techniques to form oligomers is proposed. Helical structure can be verified experimentally (using a combination of NOESY NMR structural data and restrained molecular dynamics calculations) important questions regarding the relationship between monomer structure and oligomer secondary structure will be addressed. Finally, the biological activity of folded oligocarbates will be investigated. In particular, the synthesis of a potential anti-bacterial agent and students into the membrane permeability using this class of unnatural oligomer are proposed.